When do you pull trigger on metrics surrounding NET Revenue. 

NOI equals all revenue from the property, minus all reasonably necessary operating expenses (30%).

You have less potential for 'loss', but also not as much revenue, and you would still need some workmen to do maintenance as needed.If you go with a condo, sometimes the maintenance is covered by the HOA fee.

Also check long-term rents to make sure you can cover your costs if the STR plan falls apart somehow - this gives you a backup planas for estimating revenue, I suggest looking at comps in the area using Airdna or Pricelabs.

I current work with my Father who also wants to invest in real estate and we have thought of the Idea of using some of his own companies extra revenue to invest in real estate.

Less time & energy spent on the financial side of your business means you have more time & energy to devote to those higher revenue generating activities.

You couldn’t kept your company branding in place, transitioned your entire team over and you all could’ve benefited from stock awards and revenue share just from selling homes & supporting your team!?  

Other than adding this income to our total revenue for filing at the end of the year, are there any other filing or tax requirements I should be aware of? 

Failure to do so will be an incomplete / inaccurate return.The other issue you may see is that lenders do not want to add air-bnb income because there is no 'long-term lease'(No guarantee of future revenue).make sure to shop around for a lender that will include it for DTI purposes.

Purchase price: $650,000 Cash invested: $80,000 Found this 5 family right on the MLS for $650K, needs about $50K of repair and over the course of a year, we plan to raise revenue to $8,300!